What’s your gender? Man
How old are you? 58 (24 then)
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? SoCal
Highest education received: College degree (eg., BA, BS)
What’s your occupation? IT
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Bisexual
Any other term(s) that describe your sexuality or sexual identity? Hetero relationships, gay sex only
How many sexual partners have you had in your life (including oral sex)? Over 100
How many hookup stories have you here posted before? 0

First Time Anal

How long ago did this hookup happen? 1983

What was your relationship status at the time? Engaged/Married (monogamous)

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? Just met that day

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? D was a cute 20 year old hanging out in a common cruise location in West Hollywood (this was a long time ago when that was what you did). He was there because he was looking for rent money. Luckily when he saw me he decided he could get rent money tomorrow; he wanted me today.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I had attended a late meeting up in Hollywood for a tech group I belonged to. Feeling frisky, I decided to go cruising West Hollywood to see what I could find. Luckily, I found D pretty quickly and he agreed to hop in my car.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? As soon as D got in the car, we started touching and rubbing each other. Since neither of us really had any place to go, we just drove around the area, had small talk (found out D had recently moved from Texas), and got hornier and hornier (we both had our shirts off and our hands were all over each other; we both liked the partner we had). We couldn’t find a good place to park, but took advantage of stop lights or stop signs when no one was around to kiss and further make out. We were very, very compatible in how we liked to kiss and be aroused so this was really good.

After trying street after street to find a place to park, we were a little disappointed we couldn’t find one. We really wanted to take things further than you could in a moving car, more than you could even if stopped at a light or stop sign. After 90 minutes of looking, D suggested he might know where we could go in the Hollywood Hills for some alone time. I wanted him badly, so I was game.

I followed his directions until we got to a place D felt would work. To be safe, we dropped the seats back and made out for 10-15 minutes before taking the next step. Since no one had come by in those 15 minutes, we finally felt safe to progress. I had never done anal before, but D really wanted to ride my big cock so he took off the rest of his clothes and started to mount me. Using his saliva alone he was able to get my dick all the way into his backside (bareback, sitting on my pelvis). The sensation was unbelievable.

Anal was totally new to me and I really didn’t know what it would be like. D was an excellent lover, and we kissed and rubbed while he expertly went up and down on my cock. I was in heaven, and didn’t want what I was feeling to stop. It probably wasn’t that long before I was letting D know that I was ready to explode. Since this was all new, I asked him if it was okay to cum in his ass. He assured me that was the point. Almost immediately I had one of the strongest orgasms in my life. I remember shouting as it started, as if D couldn’t tell, “I’m cuming!” I grabbed him and held him tight while he milked everything he could out of me.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? No

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? I grabbed D and pulled him close and gave him a really passionate kiss while my throbbing dick was calming down inside him. I didn’t want to let go it was that good. Only when I started to shrink (which was a surprise I was still young enough that I normally stayed hard; but this was one of my hardest orgasms) did D step out of the car, grab his clothes, and put them back on.

Once we got ourselves all back together, D hopped back in the car and we kissed some more. I knew this event was very important to me and I would never forget it. Finally I drove D back to where I originally picked him up. I parked, we both got out of the car and D wanted me to end the night as two lovers should, with another passionate kissing session. But as I said above, I am not comfortable with gay relationships and worried too much about getting caught or arrested. I did finally give a half-hearted hug as we said goodbye. I do not believe I gave him my business card so he had no way to get in touch with me nor I with him.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s)

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? No one

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? The thundering orgasm D gave me

What was the WORST thing about this hookup? I lived 40 miles away so there was no way to make this a regular thing.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Nope. Loved it before this and loved it after this. I’ve never had any restrictions on casual sex in my life.

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup? 9-12 months later, I found myself driving through West Hollywood and spotted D having dinner. I parked the car, D spotted me, and came out to join me. In a lot of ways, it seemed like he remembered our night in the same positive light I did. This time I drove him home (or near home, we parked 3 long blocks away), we walked holding hands to his place, and then we made out again. This time he topped me, but I had no idea what to do our how to be ready. Maybe I should have spoke up, but D wasn’t realizing it wasn’t good for me (I don’t think he is a good teacher like that). He did come in me bareback, I kissed him goodbye, then drove 40 miles home.

I still think of D often, and remember the “I’m coming!” like it was yesterday. Memories of that night get me off many times in the shower and other locations. I don’t get to top guys often, but I take every opportunity I can get and none of them have replaced that night at the top of the list (yet).

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? I understand the separation between relationship sex and casual sex and don’t believe they can’t both occur. Some people get this and some people don’t. And of those who might get it, not all of them are capable of separating the two so they can’t function in both circles at the same time. Having contracted HSV from my ex-wife, I have had to curb my casual activities unfortunately.

What do you think about the Casual Sex Project? I like it and love reading the stories. Makes me jealous and makes me horny. It also helps others see that this is normal.

You have a hookup story to share? Submit it here!